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US 6,720,334 B2Granted
Urea substituted imidazopyridines
Assignee3M Innovative Properties Company
InventorsJoseph F. Dellaria, Chad A. Haraldson, Philip D. Heppner, Kyle J. Lindstrom, Bryon A. Merrill
Life of this patent
Estimating the term…
Abstract
Imidazopyridine compounds that contain urea or thiourea functionality at the 1-position are useful as immune response modifiers. The compounds and compositions of the invention can induce the biosynthesis of various cytokines and are useful in the treatment of a variety of conditions including viral diseases and neoplastic diseases.
Claims40
A compound of the formula (I):
- wherein
- X is ethylene, propylene, or butylene;
- Y is —CO— or —CS—;
- Z is a —NR6—, —NR6—CO—, —NR6—SO2—, or —NR7—;
- R1 is aryl, heteroaryl, C1-10 alkyl, or C2-10 alkenyl, each of which may be unsubstituted or substituted by one or more substituents independently selected from the group consisting of:
- -alkyl;
- -aryl;
- -substituted aryl;
- -heterocyclyl;
- —O-alkyl;
- —CO—O-alkyl;
- —S(O)0-2-alkyl;
- -(alkyl)0-1—N(R6)2;
- —P(O)(O-alkyl)2;
- -halogen;
- -haloalkyl;
- -haloalkoxy;
- and
- —CN;
- R2 is selected from the group consisting of:
- -hydrogen;
- —C1-10 alkyl;
- and
- —C1-10 alkyl-O—C1-10alkyl;
- R3 and R4 are independently selected from the group consisting of hydrogen, and methyl;
- R5 is H or C1-10 alkyl, or when R5 is C1-10 alkyl and X is ethylene, propylene or butylene, R5 can join with X to form a ring that contains one nitrogen atom;
- each R6 is independently H or C1-10 alkyl;
- R7 is H or C1-10 alkyl which may be interrupted by one hetero atom, or when R1 is alkyl and R7 is C1-10 alkyl which may be interrupted by one hetero atom, R7 and R1 can join to form a ring containing one nitrogen atom and optionally one additional hetero atom;
- or a pharmaceutically acceptable salt thereof.
26 more elements
A compound selected from:
- 1-[4-(4-Amino-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl)butyl]-3-(1-methylethyl)urea;
- 1-[4-(4-Amino-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl)butyl]-3-(1,1-dimethylethyl)urea;
- 1-[4-(4-Amino-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl)butyl]-3-butylurea;
- 1-[4-(4-Amino-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl)butyl]-3-phenylurea;
- 1-[4-(4-Amino-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl)butyl]-3-cyclohexylurea
- 1-[4-(4-Amino-6,7-dimethyl-1H-imidazo[4,5-c)]pyridin-1-yl)butyl]-3-(3-cyanophenyl)urea
- 1-[4-(4-Amino-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl)butyl]-3-(3-methoxyphenyl)urea
- 1-[4-(4-Amino-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl)butyl]-3-[(1R*,2S*)-2-phenylcyclopropyl]urea;
- 1-(3-Acetylphenyl)-3-[4-(4-amino-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl)butyl]urea;
- 1-[4-(4-Amino-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl)butyl]-3-[4-(dimethylamino)phenyl]urea;
- 1-[4-(4-Amino-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl)butyl]-3-[3-(methylthio)phenyl]urea;
- 1-[4-(4-Amino-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl)butyl]-3-(2,4-(dimethoxyphenyl)urea;
- N-({[4-(4-Amino-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl)butyl]amino}carbonyl)benzenesulfonamide;
- N-({[4-(4-Amino-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl)butyl]amino}carbonyl)-4-methylbenzenesulfonamide;
- N-({[4-(4-Amino-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl)butyl]amino}carbonyl)-4-chlorobenzenesulfonamide;
- 1-[4-(4-Amino-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl)butyl]-3-methylthiourea;
- 1-[4-(4-Amino-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl)butyl]-3-phenylthiourea;
- 1-[4-(4-Amino-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl)butyl]-3-(phenylethyl)thiourea;
- and
- 1-[4-(4-Amino-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl)butyl]-3-(4-methoxyphenyl)thiourea;
- or a pharmaceutically acceptable salt thereof.
18 more elements
A compound selected from:
- 1-[4-(4-Amino-2-ethoxymethyl-6-methyl-1H-imidazo[4,5-c]pyridin-1-yl)butyl]-3-(1-methylethyl)urea;
- 1-[4-(4-Amino-2-ethoxymethyl-6-methyl-1H-imidazo[4,5-c]pyridin-1-yl)butyl]-3-(1-dimethylethyl)urea
- 1-[4-(4-Amino-2-ethoxymethyl-6-methyl-1H-imidazo[4,5-c]pyridin-1-yl)butyl]-3-butylurea;
- 1-[4-(4-Amino-2-ethoxymethyl-6-methyl-1H-imidazo[4,5-c]pyridin-1-yl)butyl]-3-phenylurea;
- {3-[4-(4-Amino-2-ethoxymethyl-6-methyl-1H-imidazo[4,5-c]pyridin-1-yl)butyl]ureido}acetic acid ethyl ester;
- 1-[4-(4-Amino-2-ethoxymethyl-6-methyl-1H-imidazo[4,5-c]pyridin-1-yl)butyl]-3-(3-cyanophenyl)urea;
- 1-[4-(4-Amino-2-ethoxymethyl-6-methyl-1H-imidazo[4,5-c]pyridin-1-yl)butyl]-3-[(1R*,2S*)-2-phenylcyclopropyl]urea;
- 1-(3-Acetylphenyl)-3-[4-(4-amino-2-ethoxymethyl-6-methyl-1H-imidazo[4,5-c]pyridin-1-yl)butyl]urea;
- 1-[4-(4-Amino-2-ethoxymethyl-6-methyl-1H-imidazo[4,5-c]pyridin-1-yl)butyl]-3-[4-(dimethylamino)phenlyl]urea;
- 1-[4-(4-Amino-2-ethoxymethyl-6-methyl-1H-imidazo[4,5-c]pyridin-1-yl)butyl]-3-[3-(methylthio)phenyl]urea;
- 1-[4-(4-Amino-2-ethoxymethyl-6-methyl-1H-imidazo[4,5-c]pyridin-1-yl)butyl]-3-(2,4-dimethoxyphenyl)urea;
- N-[({4-(4-Amino-2-(ethoxymethyl)-6-methyl-1H-imidazo[4,5-c]pyridin-1-yl]butyl}amino)carbonyl]benzenesulfonamide;
- N-[({4-(4-Amino-2-(ethoxymethyl)-6-methyl-1H-imidazo[4,5-c]pyridin-1-yl]butyl}amino)carbonyl]-4-methylbenzenesulfonamide;
- 1-[4-(4-Amino-2-ethoxymethyl-6-methyl-1H-imidazo[4,5-c]pyridin-1-yl)butyl]-3-methylthiourea;
- 1-[4-(4-Amino-2-ethoxymethyl-6-methyl-1H-imidazo[4,5-c]pyridin-1-yl)butyl]-3-phenylthiourea;
- 1-[4-(4-Amino-2-ethoxymethyl-6-methyl-1H-imidazo[4,5-c]pyridin-1-yl)butyl]-3-(2-furoyl)thiourea;
- 1-[4-(4-Amino-2-ethoxymethyl-6-methyl-1H-imidazo[4,5-c]pyridin-1-yl)butyl]-3-(2-phenylethyl)thiourea;
- and
- 1-[4-(4-Amino-2-ethoxymethyl-6-methyl-1H-imidazo[4,5-c]pyridin-1-yl)butyl]-3-(4-methoxyphenyl)thiourea;
- or a pharmaceutically acceptable salt thereof.
17 more elements
A compound selected from:
- 4-{2-[4-Amino-2-(ethoxymethyl)-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl]ethyl}-N-(1-methylethyl)piperidine-1-carboxamide;
- 4-{2-[4-Amino-2-(ethoxymethyl)-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl]ethyl}-N-(1,1-dimethylethyl)piperidine-1-carboxamide;
- 4-{2-[4-Amino-2-(ethoxymethyl)-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl]ethyl}-N-butylpiperidine-1-carboxamide;
- 4-{2-[4-Amino-2-(ethoxymethyl)-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl]ethyl}-N-phenylpiperidine-1-carboxamide;
- 4-{2-[4-Amino-2-(ethoxymethyl)-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl]ethyl}-N-cyclohexylpiperidine-1-carboxamide;
- Ethyl N-[(4-{2-[4-amino-2-(ethoxymethyl)-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl]ethyl}piperidin-1-yl)carbonyl]-glycinate;
- 4-{2-[4-Amino-2-(ethoxymethyl)-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl]ethyl}-N-(3-cyanophenyl)piperidine-1-carboxamide;
- 4-{2-[4-Amino-2-(ethoxymethyl)-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl]ethyl}-N-(3-methoxyphenyl)piperidine-1-carboxamide;
- 4-{2-[4-Amino-2-(ethoxymethyl)-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl]ethyl}-N-[(1R*,2S*)-2-phenylcyclopropyl[piperidine-1-carboxamide;
- N-(3-Acetylphenyl)-4-{2-[4-amino-2-(ethoxymethyl)-6,7-dimethyl-1H-imidazo[4,5-C]pyridin-1-yl]ethyl}piperidine-1-carboxamide;
- 4-{2-[4-Amino-2-(ethoxymethyl)-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl]ethyl}-N-[4-(dimethylamino)phenyl]piperidine-1-carboxamide;
- 4-{2-[4-Amino-2-(ethoxymethyl)-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl]ethyl}-N-]3-(methylthio)phenyl]piperidine-1-carboxamide;
- 4-{2-[4-Amino-2-(ethoxymethyl)-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl]ethyl}-N-methyl-N-phenylpiperidine-1-carboxamide;
- 4-{2-[4-Amino-2-(ethoxymethyl)-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl]ethyl}-N-(2,4-dimethoxyphenyl)piperidine-1-carboxamide;
- N-[(4-{2-[4-Amino-2-(ethoxymethyl)-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl]ethyl}piperidin-1-yl)carbonyl]benzenesulfonamide;
- N-[(4-{2-[4-Amino-2-(ethoxymethyl)-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl]ethyl}piperidin-1-yl)carbonyl]-4-chlorobenzenesulfonamide;
- 4-{2-[4-Amino-2-(ethoxymethyl)-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl]ethyl}-N-phenylpiperidine-1-carbothioamide;
- N-[(4-{2-[4-Amino-2-(ethoxymethyl)-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl]ethyl}piperidin-1-yl)carbonothioyl]-2-furamide;
- 4-{2-[4-Amino-2-(ethoxymethyl)-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl]ethyl}-N-(2-phenylethyl)piperidine-1-carbothioamide;
- and
- 4-{2-[4-Amino-2-(ethoxymethyl)-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl]ethyl}-N-(4-methoxyphenyl)piperidine-1-carbothioamide;
- or a pharmaceutically acceptable salt thereof.
19 more elements
A compound selected from:
- 1-[3-(4-Amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)propyl]-3-(1-methylethyl)urea;
- 1-[3-(4-Amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)propyl]-3-butylurea;
- 1-[3-(4-Amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)propyl]-3-phenylurea;
- 1-[3-(4-Amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)propyl]-3-cyclohexylurea;
- {3-[3-(4-Amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)propyl]urea) acetic acid ethyl ester;
- 1-[3-(4-Amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)propyl]-3-(3-cyanophenyl)urea;
- 1-[3-(4-Amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)propyl]-3-(3-methoxyphenyl)urea;
- 1-[3-(4-Amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)propyl]-3-[(1R*,2S*)-2-phenylcyclopropyl]urea;
- 1-(3-Acetylphenyl)-3-[3-(4-amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)propyl]urea;
- 1-[3-(4-Amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)propyl]-3-[4-(dimethylamino)phenyl]urea;
- 1-[3-(4-Amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)propyl]-3-[3-(methylthio)phenyl]urea;
- 3-[3-(4-Amino-2,6,7-trimethyl 1H-imidazo[4,5-c]pyridin-1-yl)propyl]-1-methyl-1-phenylurea;
- 1-[3-(4-Amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)propyl]-3-(2,4-dimethoxyphenyl)urea;
- N-({[3-(4-Amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)propyl]amino}carbonyl)-4-methylbenzenesulfonamide;
- N-({[3-(4-Amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)propyl]amino}carbonyl)-2-chlorobenzenesulfonamide;
- 1-[3-(4-Amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)propyl]-3-phenylthiourea;
- 1-[3-(4-Amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)propyl]-3-(2-furoyl)thiourea;
- 1-[3-(4-Amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)propyl]-3-(2-phenylethyl)thiourea;
- and
- 1-[3-(4-Amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)propyl]-3-(4-methoxyphenyl)thiourea;
- or a pharmaceutically acceptable salt thereof.
18 more elements
A compound selected from:
- 3-[3-(4-Amino-2-ethoxymethyl-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl)propyl]-1,1-dimethylurea;
- 1-[3-(4-Amino-2-ethoxymethyl-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl)propyl]-3-(1-methylethyl)urea;
- 1-[3-(4-Amino-2-ethoxymethyl-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl)propyl]-3-(1-dimethylethyl)urea;
- 1-[3-(4-Amino-2-ethoxymethyl-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl)propyl]-3-butylurea;
- 1-[3-(4-Amino-2-ethoxymethyl-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl)propyl]-3-phenylurea;
- 1-[3-(4-Amino-2-ethoxymethyl-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl)propyl]-3-cyclohexylurea;
- {3-[3-(4-Amino-2-ethoxymethyl-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl)propyl]ureido}acetic acid ethyl ester;
- 1-[3-(4-Amino-2-ethoxymethyl-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl)propyl]-3-(3-cyanophenyl)urea;
- 1-[3-(4-Amino-2-ethoxymethyl-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl)propyl]-3-(3-methoxyphenyl)urea;
- 1-[3-(4-Amino-2-ethoxymethyl-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl)propyl]-3-[(1R*,2S*)-2-phenylcyclopropyl]urea;
- 1-(3-Acetylphenyl)-3-[3-(4-amino-2-ethoxymethyl-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl)propyl]urea;
- 1-[3-(4-Amino-2-ethoxymethyl-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl)propyl]-3-[4-(dimethylamino)phenyl]urea;
- 1-[3-(4-Amino-2-ethoxymethyl-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl)propyl]-3-[3-(methylthio)phenyl]urea;
- 3-[3-(4-Amino-2-ethoxymethyl-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl)propyl]-1-methyl-1-phenylurea;
- 1-[3-(4-Amino-2-ethoxymethyl-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl)propyl]-3-(4-trifluoromethylphenyl)urea;
- N-[({3-[4-Amino-2-ethoxymethyl-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl]propyl}amino)carbonyl]benzenesulfonamide;
- N-[({3-[4-Amino-2-ethoxymethyl-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl]propyl}amino)carbonyl]benzenesulfonamide;
- N-[({3-[4-Amino-2-ethoxymethyl-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl]propyl}amino)carbonyl]-4-methylbenzenesulfonamide;
- N-[({3-[4-Amino-2-ethoxymethyl-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl]propyl}amino)carbonyl]-2-chlorobenzenesulfonamide;
- 1-[3-(4-Amino-2-ethoxymethyl-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl)propyl]-3-[3-(diethylamino)propyl]thiourea;
- 1-[3-(4-Amino-2-ethoxymethyl-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl)propyl]-3-(4-phenylthiourea;
- 1-[3-(4-Amino-2-ethoxymethyl-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl)propyl]-3-furoyl)thiourea;
- 1-[3-(4-Amino-2-ethoxymethyl-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl)propyl]-3-(2-morpholin-4-ylethyl)thiourea;
- and
- 1-[3-(4-Amino-2-ethoxymethyl-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl)propyl]-3-(4-methoxyphenyl)thiourea;
- or a pharmaceutically acceptable salt thereof.
23 more elements
A compound selected from:
- 3-[2-(4-Amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)ethyl]-1,1-dimethylurea;
- 1-[2-(4-Amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)ethyl]-3-(1-methylethyl)urea;
- 1-[2-(4-Amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)ethyl]-3-(1,1-dimethylethyl)urea;
- 1-[2-(4-Amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)ethyl]-3-butylurea;
- 1-[2-(4-Amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)ethyl]-3-phenylurea;
- 1-[2-(4-Amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)ethyl]-3-cyclohexylurea;
- {3-[2-(4-Amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)ethyl]ureido}acetic acid ethyl ester;
- 1-[2-(4-Amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)ethyl]-3-(3-cyanophenyl)urea;
- 1-[2-(4-Amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)ethyl]-3-(3-methoxyphenyl)urea;
- 1-[2-(4-Amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)ethyl]-3-[1R*,2S*)-2-phenylcyclopropyl]urea;
- 1-(3-Acetylphenyl)-3-[-(4-amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl]ethyl]urea;
- 1-[2-(4-Amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)ethyl]-3-[4-(dimethylamino)phenyl]urea;
- 1-[2-(4-Amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)ethyl]-3-[3-(methylthio)phenyl]urea;
- 3-[2-(4-Amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)ethyl]-1-methyl-1-phenylurea;
- 1-[2-(4-Amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)ethyl]-3-(4-trifluoromethylphenyl)urea;
- 1-[2-(4-Amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)ethyl]-3-benzoylurea;
- 1-Adamantan-1-yl-3-[2-(4-amino-2,6,7-trimethyl-1-H-imidazo[4,5-c]pyridin-1-yl)ethyl]urea;
- Diethyl {[2-(4-amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)ethyl]amino}carbonylamidophosphate;
- 1-[2-(4-Amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)ethyl]-3-(4-phenoxyphenyl)urea;
- N-({-[2-(4-Amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)ethyl]amino) carbonyl)benzenesulfonamide;
- N-({-[2-(4-Amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)ethyl]amino}carbonyl)-2chlorobenzenesulfonamide;
- 1-[2-(4-Amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)ethyl]-3-[3-(diethylamino)propyl]thiourea;
- 1-[2-(4-Amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)ethyl]-3-phenylthiourea;
- 1-[2-(4-Amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)ethyl]-3-(2-furoyl)thiourea;
- 1-[2-(4-Amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)ethyl]-3-(2-morpholin-4-ylethyl)thiourea;
- 1-[2-(4-Amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)ethyl]-3-(4-methoxyphenyl)thiourea;
- 1-[2-(4-Amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)ethyl]-3-benzoylthiourea;
- and
- 1-Adamantan-1-yl-3-[2-(4-amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)ethyl]thiourea;
- or a pharmaceutically acceptable salt thereof.
27 more elements
A compound selected from:
- 3[4-(4-Amino-2-ethoxymethyl-7-methyl-1H-imidazo[4,5-c]pyridin-1-yl)butyl]1,1-dimethylurea;
- 1-[4-(4-Amino-2-ethoxymethyl-7-methyl-1H-imidazo[4,5-c]pyridin-1-yl)butyl]-3-(1-methylethyl)urea;
- 1-[4-(4-Amino-2-ethoxymethyl-7-methyl-1H-imidazo[4,5-c]pyridin-1-yl)butyl]-3-(1-dimethylethyl)urea;
- 1-[4-(4-Amino-2-ethoxymethyl-7-methyl-1H-imidazo[4,5-c]pyridin-1-yl)butyl]-3-butylurea;
- 1-[4-(4-Amino-2-ethoxymethyl-7-methyl-1H-imidazo[4,5-c]pyridin-1-yl)butyl]-3-phenylurea;
- 1-[4-(4-Amino-2-ethoxymethyl-7-methyl-1H-imidazo[4,5-c]pyridin-1-yl)butyl]-3-cyclohexylurea;
- {3-[4-(4-Amino-2-ethoxymethyl-7-methyl-1H-imidazo[4,5-c]pyridin-1-yl)butyl]ureido}acetic acid ethyl ester;
- 1-[4-(4-Amino-2-ethoxymethyl-7-methyl-1H-imidazo[4,5-c]pyridin-1-yl)butyl]-3-(3-cyanophenyl)urea;
- 1-[4-(4-Amino-2-ethoxymethyl-7-methyl-1H-imidazo[4,5-c]pyridin-1-yl)butyl]-3-(3-methoxyphenyl)urea;
- 1-[4-(4-Amino-2-ethoxymethyl-7-methyl-1H-imidazo[4,5-c]pyridin-1-yl)butyl]-3-[(1R*,2S*)-2-phenylcyclopropyl]urea;
- 1-(3-Acetylphenyl)-3-[4-(4-amino-2-ethoxymethyl-7-methyl-1H-imidazo[4,5-c]pyridin-1-yl)butyl]urea;
- 1-[4-(4-Amino-2-ethoxymethyl-7-methyl-1H-imidazo[4,5-c]pyridin-1-yl)butyl]-3-[4-(dimethylamino)phenyl]urea;
- 1-[4-(4-Amino-2-ethoxymethyl-7-methyl-1H-imidazo[4,5-c]pyridin-1-yl)butyl]-3-[3-(methylthio)phenyl]urea;
- 3-[4-(4-Amino-2-ethoxymethyl-7-methyl-1H-imidazo[4,5-c]pyridin-1-yl)butyl]-1-(1-methyl-1-phenylurea;
- 1-[4-(4-Amino-2-ethoxymethyl-7-methyl-1H-imidazo[4,5-c]pyridin-1-yl)butyl]-3-(4-trifluoromethylphenyl)-urea;
- 1-Adamantan-1-yl-3[4-(4-amino-2-ethoxymethyl-7-methyl-1H-imidazo[4,5-c]pyridin-1-yl)butyl]urea;
- 3-{3-[4-(4-Amino-2-ethoxymethyl-7-methyl-1H-imidazo[4,5-c]pyridin-1-yl)butyl-ureido}benzoic acid ethyl ester;
- 1-[4-(4-Amino-2-ethoxymethyl-7-methyl-1H-imidazo[4,5-c]pyridin-1-yl)butyl]-3-[1-(1-naphthyl)ethyl]urea;
- 1-[4-(4-Amino-2-ethoxymethyl-7-methyl-1H-imidazo[4,5-c]pyridin-1-yl)butyl]-3-(4-phenoxyphenyl)urea;
- N-[({4-[4-Amino-2-(ethoxymethyl)-7-methyl-1H-imidazo[4,5-c]pyridin-1-yl]butyl}amino)carbonyl]-4-methylbenzenesulfonamide;
- N-[({4-[4-Amino-2-(ethoxymethyl)-7-methyl-1H-imidazo[4,5-c]pyridin-1-yl]butyl}amino)carbonyl]-2-chlorobenzenesulfonamide;
- 1-[4-(4-Amino-2-ethoxymethyl-7-methyl-1H-imidazo[4,5-c]pyridin-1-yl)butyl]-3-[3-(diethylamino)propyl]thiourea;
- 1-[4-(4-Amino-2-ethoxymethyl-7-methyl-1H-imidazo[4,5-c]pyridin-1-yl)butyl]-3-phenylthiourea;
- 1-[4-(4-Amino-2-ethoxymethyl-7-methyl-1H-imidazo[4,5-c]pyridin-1-yl)butyl]-3-(2-furoyl)thiourea;
- 1-[4-(4-Amino-2-ethoxymethyl-7-methyl-1H-imidazo[4,5-c]pyridin-1-yl)butyl]-3-(2-morpholin-4-ylethyl)thiourea;
- 1-[4-(4-Amino-2-ethoxymethyl-7-methyl-1H-imidazo[4,5-c]pyridin-1-yl)butyl]-3-(4-methoxyphenyl)thiourea;
- 1-[4-(4-Amino-2-ethoxymethyl-7-methyl-1H-imidazo[4,5-c)pyridin-1-yl)butyl]-3-benzoylthiourea;
- 1-Adamantan-1-yl-3-[4-(4-amino-2-ethoxymethyl-7-methyl-1H-imidazo[4,5-c]pyridin-1-yl)butyl]thiourea;
- and
- 4-{3-[4-(4-Amino-2-ethoxymethyl-7-methyl-1H-imidazo[4,5-c]pyridin-1-yl)-butyl]thioureido}benzenesulfonamide;
- or a pharmaceutically acceptable salt thereof.
28 more elements
Dependencies are inferred from the claim text.